Founder Spotlight: Dave Benson

Reimagining Fan Connection One Minute at a Time

Dave Benson has spent his career at the intersection of sports, technology, and storytelling. From shaping global fan engagement strategies at some of the world’s biggest media brands to launching a startup that redefines how fans connect with teams and athletes, Dave’s work is guided by one simple belief: the most powerful moments are often the shortest and the most human.

As Founder and CEO of SuperQuickQuestion, Dave is transforming the traditional meet-and-greet into something more genuine, scalable, and meaningful. The platform enables live, one-on-one video chats capped at 60 seconds, creating intimate, time-bound interactions that feel exclusive without being inaccessible.

For fans, it’s a real moment of connection. For teams and sponsors, it’s a powerful new engagement and revenue tool; one already trusted by major global brands.

From Big Media to Small Moments

Dave’s path to entrepreneurship is anything but linear and that’s exactly what makes it compelling.

Before founding SuperQuickQuestion, Dave built a career leading content and engagement strategies at IBM, ESPN, Major League Baseball, and Bleacher Report. He served as Creative Director for MLB’s Fan Cave, a groundbreaking fan engagement campaign that generated more than 1 billion impressions and helped redefine how leagues interact with digital audiences.

At Bleacher Report, Dave led content teams responsible for 300 million impressions, oversaw major audience growth initiatives, and helped launch the company’s full-length documentary division. Along the way, his work earned industry recognition including a Digiday Award, Shorty Award, Webby, Cynopsis Award, and a New York Association of Black Journalists Award—not to mention the timeless accolade of being voted “funniest” in high school.

Yet despite the scale and success, Dave kept noticing the same frustration across organizations: too much noise, too little listening.

Finding the Opportunity in Friction

SuperQuickQuestion was born from observing everyday business and fan interactions that felt transactional, awkward, or simply ineffective. Dave recognized a gold mine in solving these frustrations—not by adding more features, but by doing less, exceptionally well.

The insight was simple but powerful: people want to be heard, and constraints can create better conversations. A 60-second limit removes pressure, eliminates small talk, and forces clarity—resulting in more authentic exchanges.

This philosophy extends beyond the product itself. Dave emphasizes the transformative power of listening, especially in early sales meetings. Rather than pitching immediately, SuperQuickQuestion focuses on understanding real needs first, an approach that has helped the platform resonate with teams, sponsors, and fans alike.

Ephemeral Moments, Lasting Impact

At its core, SuperQuickQuestion is about creating ephemeral, synchronous shared moments—interactions that exist only in real time, but leave a lasting impression. These brief exchanges foster trust, authenticity, and emotional connection in ways that asynchronous content often can’t.

The platform’s branding and revenue model allow teams and sponsors to deliver these moments in a way that feels personal while remaining scalable and mutually beneficial. That approach has attracted major partners, including Pepsi and Verizon, with Verizon activating SuperQuickQuestion around the Super Bowl for the second year in a row, a powerful signal of the platform’s value at the highest levels of sport and brand engagement.

Looking Ahead

As SuperQuickQuestion continues to grow, Dave remains focused on one thing: making interactions better by making them simpler. In a world obsessed with scale, his work is a reminder that intimacy—when thoughtfully designed—can scale too. And sometimes, sixty seconds is all it takes.